Table of contents

1. A Review of General Chemistry5h 5m
2. Molecular Representations1h 14m
3. Acids and Bases2h 46m
4. Alkanes and Cycloalkanes4h 17m
5. Chirality3h 39m
6. Thermodynamics and Kinetics1h 22m
7. Substitution Reactions1h 48m
8. Elimination Reactions2h 30m
9. Alkenes and Alkynes2h 9m
10. Addition Reactions3h 19m
11. Radical Reactions1h 58m
12. Alcohols, Ethers, Epoxides and Thiols2h 42m
13. Alcohols and Carbonyl Compounds2h 17m
14. Synthetic Techniques1h 26m
15. Analytical Techniques:IR, NMR, Mass Spect7h 3m
16. Conjugated Systems6h 13m
17. Ultraviolet Spectroscopy51m
18. Aromaticity2h 34m
19. Reactions of Aromatics: EAS and Beyond5h 1m
20. Phenols55m
21. Aldehydes and Ketones: Nucleophilic Addition4h 56m
22. Carboxylic Acid Derivatives: NAS2h 51m
23. The Chemistry of Thioesters, Phophate Ester and Phosphate Anhydrides1h 10m
24. Enolate Chemistry: Reactions at the Alpha-Carbon1h 53m
25. Condensation Chemistry2h 9m
26. Amines1h 43m
27. Heterocycles2h 0m
28. Carbohydrates5h 53m
29. Amino Acids4h 20m
30. Peptides and Proteins2h 42m
31. Catalysis in Organic Reactions1h 30m
32. Lipids 2h 50m
33. The Organic Chemistry of Metabolic Pathways2h 52m
34. Nucleic Acids1h 32m
35. Transition Metals6h 14m
36. Synthetic Polymers1h 49m

26. Amines

Reductive Amination

Organic Chemistry

26. Amines

Reductive Amination

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7:38 minutes

Problem 19

Textbook Question

Show how you would use the same sulfonyl chloride as used in the sulfanilamide synthesis to make sulfathiazole and sulfapyridine.

Verified step by step guidance

Step 1: Begin with the sulfonyl chloride used in the sulfanilamide synthesis, which is typically p-aminobenzenesulfonyl chloride (C6H4(SO2Cl)(NH2)). This compound contains both an amino group (-NH2) and a sulfonyl chloride group (-SO2Cl).

Step 2: To synthesize sulfathiazole, react the sulfonyl chloride with 2-aminothiazole. The reaction involves nucleophilic substitution where the amino group of 2-aminothiazole attacks the sulfur atom of the sulfonyl chloride, displacing the chloride ion (Cl⁻). This forms the sulfonamide bond (-SO2NH-).

Step 3: To synthesize sulfapyridine, react the sulfonyl chloride with 2-aminopyridine. Similar to the previous step, the amino group of 2-aminopyridine acts as a nucleophile and attacks the sulfur atom of the sulfonyl chloride, displacing the chloride ion and forming the sulfonamide bond (-SO2NH-).

Step 4: Ensure the reaction conditions are appropriate for nucleophilic substitution. Typically, the reaction is carried out in a polar aprotic solvent like acetone or DMF, and a base such as pyridine or triethylamine is added to neutralize the HCl byproduct.

Step 5: After the reaction, purify the products (sulfathiazole and sulfapyridine) using techniques such as recrystallization or chromatography to isolate the desired compounds and remove any impurities.

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Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Sulfonyl Chlorides

Sulfonyl chlorides are reactive compounds containing a sulfonyl group (SO2) bonded to a chlorine atom. They are commonly used in organic synthesis to introduce sulfonyl groups into various substrates. In the context of sulfanilamide synthesis, sulfonyl chlorides can react with amines to form sulfonamides, which are key components in the synthesis of antibiotics like sulfathiazole and sulfapyridine.

Sulfanilamide Derivatives

Sulfanilamide derivatives are a class of sulfonamide antibiotics that contain an amine group attached to a sulfonyl group. These compounds are synthesized by reacting sulfonyl chlorides with appropriate amines. Understanding the structure and reactivity of sulfanilamide derivatives is crucial for modifying them to create new antibiotics, such as sulfathiazole and sulfapyridine, which have specific therapeutic properties.

Nucleophilic Substitution Reactions

Nucleophilic substitution reactions involve the replacement of a leaving group in a molecule by a nucleophile. In the case of sulfonyl chlorides, the chlorine atom acts as a leaving group, allowing nucleophiles like amines to attack the sulfonyl carbon. This reaction is fundamental in the synthesis of sulfanilamide derivatives, as it enables the formation of new bonds and the introduction of functional groups necessary for the desired antibiotic properties.

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Textbook Question

Show how to synthesize the following amines from the indicated starting materials by reductive amination.

(a) benzylmethylamine from benzaldehyde

(b) N-benzylpiperidine from piperidine

Textbook Question

Using cyclohexanone as the starting material, describe how each of the following compounds can be synthesized:

Textbook Question

Show how m-toluidine can be converted to the following compounds, using any necessary reagents.

(f)

Textbook Question

Using any necessary reagents, show how you would accomplish the following syntheses.

(d)

Textbook Question

Predict the products of the following reactions:

(h)

Textbook Question

Show how to synthesize the following amines from the indicated starting materials by reductive amination.

(e)

Textbook Question

Show how you can synthesize the following tertiary amine three different ways, each using a different secondary amine and adding the final substituent by

(a) reductive amination (3 ways).

Textbook Question

Show how you can synthesize the following compounds starting with benzene, toluene, and alcohols containing no more than four carbon atoms as your organic starting materials. Assume that para is the major product (and separable from ortho) in ortho, para mixtures.

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